N-(4-pyrrolidinyl-2-butynyl)-3-methyl-2-azetidinone | 124443-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: N-(4-pyrrolidinyl-2-butynyl)-3-methyl-2-azetidinone
• 英文别名: 3-Methyl-1-(4-pyrrolidin-1-ylbut-2-ynyl)azetidin-2-one
• CAS: 124443-37-4
• 化学式: C₁₂H₁₈N₂O
• 分子量: 206.288
• InChiKey: XEJJTPWBJQDUEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  四氢吡咯 、 聚合甲醛 、 N-(2-丙炔基)-3-甲基-2-氮杂环丁酮 在 copper(l) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 以96%的产率得到N-(4-pyrrolidinyl-2-butynyl)-3-methyl-2-azetidinone
  参考文献：
  名称：

  .beta.-Lactam analogs of oxotremorine. 3- and 4-Methyl-substituted 2-azetidinones

  摘要：

  Four beta-lactam analogues (8-11) of oxotremorine were synthesized and assayed for muscarinic and antimuscarinic activity on the isolated guinea pig ileum. The pharmacological results were compared with those obtained previously with the beta-lactam analogue 7 and the 3-, 4-, and 5-methyl-substituted 2-pyrrolidones 2-6. The new compounds were less potent than the corresponding 2-pyrrolidones, regardless of whether they showed agonist (10 and 11), partial agonist (8), or antagonist properties (9) in the ileum assay. The agonists 10 and 11 were about 200-fold less potent than 7. Compounds 8-11 also were less potent than the similarly substituted 2-pyrrolidones in inhibiting the binding of the muscarinic antagonist (-)-[3H]-N-methylscopolamine in homogenates of the rat cerebral cortex.

  DOI：

  10.1021/jm00164a018

文献信息

• NILSSON, BJORN M.;RINGDAHL, BJORN;HACKSELL, ULI, J. MED. CHEM., 33,(1990) N, C. 580-584
  作者：NILSSON, BJORN M.、RINGDAHL, BJORN、HACKSELL, ULI

  DOI：——

  日期：——
• .beta.-Lactam analogs of oxotremorine. 3- and 4-Methyl-substituted 2-azetidinones
  作者：Bjoern M. Nilsson、Bjorn Ringdahl、Uli Hacksell

  DOI：10.1021/jm00164a018

  日期：1990.2

  Four beta-lactam analogues (8-11) of oxotremorine were synthesized and assayed for muscarinic and antimuscarinic activity on the isolated guinea pig ileum. The pharmacological results were compared with those obtained previously with the beta-lactam analogue 7 and the 3-, 4-, and 5-methyl-substituted 2-pyrrolidones 2-6. The new compounds were less potent than the corresponding 2-pyrrolidones, regardless of whether they showed agonist (10 and 11), partial agonist (8), or antagonist properties (9) in the ileum assay. The agonists 10 and 11 were about 200-fold less potent than 7. Compounds 8-11 also were less potent than the similarly substituted 2-pyrrolidones in inhibiting the binding of the muscarinic antagonist (-)-[3H]-N-methylscopolamine in homogenates of the rat cerebral cortex.